Supramolecular isomerism in caviplexes

Angewandte Chemie - International Edition

Volumn 38, Issue 17, 1999, Pages 2600-2602

  Ma, Shihong ^a   Rudkevich, Dmitry M ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Cavitands; Encapsulation hydrogen bonds; Stereoisomerism

Indexed keywords

ADAMANTANE DERIVATIVE; ALICYCLIC COMPOUND;

ARTICLE; BINDING AFFINITY; CATALYSIS; COMPLEX FORMATION; COVALENT BOND; DIASTEREOISOMER; ELECTRON TRANSPORT; HYDROGEN BOND; METHYLATION; MOLECULAR MODEL; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS; TEMPERATURE;

EID: 0033520285     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990903)38:17<2600::AID-ANIE2600>3.0.CO;2-T     Document Type: Article

References (39)

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4. For the early example of orientational isomerism in speleands see: J. Canceill, A. Collet, J. Gahard, F. Kotzyba-Hibert, J.-M. Lehn, Helv. Chim. Acta 1982, 65, 1894-1897; in carceplexes; a) P. Timmerman, W. Verboom, F. C. J. M. van Veggel, J. P. M. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) J. R. Fraser, B. Borecka, J. Trotter, J. C. Sherman, J. Org. Chem. 1995, 60, 1207-1213; c) A. M. A. van Wageningen, P. Timmerman, J. P. M. van Duynhoven, W. Verboom, F. C. J. M. van Veggel, D. N. Reinhoudt, Chem. Eur. J. 1997, 3, 639-654; see also: J. C. Sherman, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2194-2204.
5. For the early example of orientational isomerism in speleands see: J. Canceill, A. Collet, J. Gahard, F. Kotzyba-Hibert, J.-M. Lehn, Helv. Chim. Acta 1982, 65, 1894-1897; in carceplexes; a) P. Timmerman, W. Verboom, F. C. J. M. van Veggel, J. P. M. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) J. R. Fraser, B. Borecka, J. Trotter, J. C. Sherman, J. Org. Chem. 1995, 60, 1207-1213; c) A. M. A. van Wageningen, P. Timmerman, J. P. M. van Duynhoven, W. Verboom, F. C. J. M. van Veggel, D. N. Reinhoudt, Chem. Eur. J. 1997, 3, 639-654; see also: J. C. Sherman, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2194-2204.
6. For the early example of orientational isomerism in speleands see: J. Canceill, A. Collet, J. Gahard, F. Kotzyba-Hibert, J.-M. Lehn, Helv. Chim. Acta 1982, 65, 1894-1897; in carceplexes; a) P. Timmerman, W. Verboom, F. C. J. M. van Veggel, J. P. M. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) J. R. Fraser, B. Borecka, J. Trotter, J. C. Sherman, J. Org. Chem. 1995, 60, 1207-1213; c) A. M. A. van Wageningen, P. Timmerman, J. P. M. van Duynhoven, W. Verboom, F. C. J. M. van Veggel, D. N. Reinhoudt, Chem. Eur. J. 1997, 3, 639-654; see also: J. C. Sherman, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2194-2204.
7. For the early example of orientational isomerism in speleands see: J. Canceill, A. Collet, J. Gahard, F. Kotzyba-Hibert, J.-M. Lehn, Helv. Chim. Acta 1982, 65, 1894-1897; in carceplexes; a) P. Timmerman, W. Verboom, F. C. J. M. van Veggel, J. P. M. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) J. R. Fraser, B. Borecka, J. Trotter, J. C. Sherman, J. Org. Chem. 1995, 60, 1207-1213; c) A. M. A. van Wageningen, P. Timmerman, J. P. M. van Duynhoven, W. Verboom, F. C. J. M. van Veggel, D. N. Reinhoudt, Chem. Eur. J. 1997, 3, 639-654; see also: J. C. Sherman, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2194-2204.
8. For the early example of orientational isomerism in speleands see: J. Canceill, A. Collet, J. Gahard, F. Kotzyba-Hibert, J.-M. Lehn, Helv. Chim. Acta 1982, 65, 1894-1897; in carceplexes; a) P. Timmerman, W. Verboom, F. C. J. M. van Veggel, J. P. M. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) J. R. Fraser, B. Borecka, J. Trotter, J. C. Sherman, J. Org. Chem. 1995, 60, 1207-1213; c) A. M. A. van Wageningen, P. Timmerman, J. P. M. van Duynhoven, W. Verboom, F. C. J. M. van Veggel, D. N. Reinhoudt, Chem. Eur. J. 1997, 3, 639-654; see also: J. C. Sherman, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2194-2204.
9. For the early example of orientational isomerism in speleands see: J. Canceill, A. Collet, J. Gahard, F. Kotzyba-Hibert, J.-M. Lehn, Helv. Chim. Acta 1982, 65, 1894-1897; in carceplexes; a) P. Timmerman, W. Verboom, F. C. J. M. van Veggel, J. P. M. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) J. R. Fraser, B. Borecka, J. Trotter, J. C. Sherman, J. Org. Chem. 1995, 60, 1207-1213; c) A. M. A. van Wageningen, P. Timmerman, J. P. M. van Duynhoven, W. Verboom, F. C. J. M. van Veggel, D. N. Reinhoudt, Chem. Eur. J. 1997, 3, 639-654; see also: J. C. Sherman, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2194-2204.
10. a) M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668;
11. b) J. de Mendoza, Chem. Eur. J. 1998, 4, 1373-1377.
12. a) R. G. Chapman, G. Olovsson, J. Trotter, J. C. Sherman, J. Am. Chem. Soc. 1998, 120, 6252-6260;
13. b) T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Nature 1998, 394, 764-766.
14. Kinetically stable complexes with cyclodextrins; a) H. Yonemura, M. Kasahara, H. Saito, H. Nakamura, T. Matsuo, J. Phys. Chem. 1992, 96, 5765-5770; b) U. Berg, M. Gustavsson, N. Åström, J. Am. Chem. Soc. 1995, 117, 2114- 2115, and references therein; review: H.-J. Schneider, F. Hacket, V. Rüdiger, Chem. Rev. 1998, 98, 1755-1785; cyclophane diastereomerism: T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555.
15. Kinetically stable complexes with cyclodextrins; a) H. Yonemura, M. Kasahara, H. Saito, H. Nakamura, T. Matsuo, J. Phys. Chem. 1992, 96, 5765-5770; b) U. Berg, M. Gustavsson, N. Åström, J. Am. Chem. Soc. 1995, 117, 2114-2115, and references therein; review: H.-J. Schneider, F. Hacket, V. Rüdiger, Chem. Rev. 1998, 98, 1755-1785; cyclophane diastereomerism: T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555.
16. Kinetically stable complexes with cyclodextrins; a) H. Yonemura, M. Kasahara, H. Saito, H. Nakamura, T. Matsuo, J. Phys. Chem. 1992, 96, 5765-5770; b) U. Berg, M. Gustavsson, N. Åström, J. Am. Chem. Soc. 1995, 117, 2114- 2115, and references therein; review: H.-J. Schneider, F. Hacket, V. Rüdiger, Chem. Rev. 1998, 98, 1755-1785; cyclophane diastereomerism: T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555.
17. Kinetically stable complexes with cyclodextrins; a) H. Yonemura, M. Kasahara, H. Saito, H. Nakamura, T. Matsuo, J. Phys. Chem. 1992, 96, 5765-5770; b) U. Berg, M. Gustavsson, N. Åström, J. Am. Chem. Soc. 1995, 117, 2114- 2115, and references therein; review: H.-J. Schneider, F. Hacket, V. Rüdiger, Chem. Rev. 1998, 98, 1755-1785; cyclophane diastereomerism: T. H. Webb, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 8554-8555.
18. Reviews on cavitands: ref. [1a], pp. 85-130. See also: P. Timmerman, W. Verboom, D. N. Reinhoudt, Tetrahedron 1996, 52, 2663-2704.
19. Reviews on cavitands: ref. [1a], pp. 85-130. See also: P. Timmerman, W. Verboom, D. N. Reinhoudt, Tetrahedron 1996, 52, 2663-2704.
20. D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1997, 119, 9911-9912; D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 12216-12225. Another example in resorcinarene host - guest chemistry was reported by Aoyama et al.: a) Y. Kikuchi, Y. Kato, Y. Tanaka, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1991, 113, 1349-1354; b) K. Kobayashi, Y. Asakawa, Y. Kikuchi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1993, 115, 2648- 2654.
21. D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1997, 119, 9911-9912; D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 12216-12225. Another example in resorcinarene host - guest chemistry was reported by Aoyama et al.: a) Y. Kikuchi, Y. Kato, Y. Tanaka, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1991, 113, 1349-1354; b) K. Kobayashi, Y. Asakawa, Y. Kikuchi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1993, 115, 2648- 2654.
22. D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1997, 119, 9911-9912; D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 12216-12225. Another example in resorcinarene host - guest chemistry was reported by Aoyama et al.: a) Y. Kikuchi, Y. Kato, Y. Tanaka, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1991, 113, 1349-1354; b) K. Kobayashi, Y. Asakawa, Y. Kikuchi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1993, 115, 2648- 2654.
23. D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1997, 119, 9911-9912; D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 12216-12225. Another example in resorcinarene host - guest chemistry was reported by Aoyama et al.: a) Y. Kikuchi, Y. Kato, Y. Tanaka, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1991, 113, 1349-1354; b) K. Kobayashi, Y. Asakawa, Y. Kikuchi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1993, 115, 2648-2654.
24. 12]mesitylene at 295 K.
25. For complexes within complexes see: T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 1206-1209; Angew. Chem. Int. Ed. 1999, 38, 1136-1139.
26. For complexes within complexes see: T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 1206-1209; Angew. Chem. Int. Ed. 1999, 38, 1136-1139.
27. 5 could also be detected. For a discussion of phenol-amine complexes see: T. Mizutani, H. Takagi, Y. Ueno, T. Horiguchi, K. Yamamura, H. Ogoshi, J. Phys. Org. Chem. 1998, 11, 737-742.
28. Molecular modeling was performed by using the Amber* force field in the MacroModel 5.5 program: F. Mohamadi, N. G. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
29. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425-430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
30. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
31. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.-L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
32. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
33. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728-732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
34. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
35. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
36. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
37. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
38. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.
39. For leading references in chemical switching see: a) S. Shinkai, Pure Appl. Chem. 1987, 59, 425- 430; b) R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137; c) D.- L. Jiang, T. Aida, Nature 1997, 388, 454-456; d) D. A. Leigh, A. Murphy, J. P. Smart, A. M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728- 732; e) A. S. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093; d) C. Gong, H. W. Gibson, Angew. Chem. 1997, 109, 2426-2428; Angew. Chem. Int. Ed. Engl. 1997, 36, 2331-2333; f) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858; g) A. Archut, F. Vögtle, L. De Cola, G. Camillo Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699-706; review: B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993 49, 8267-8310.